ProtonMail Five Years Later, Part III: Security Features

I have been using ProtonMail full-time for over five years, and recommending it for almost six. This blog is littered with references to it, along with several incremental updates. A lot has changed since ProtonMail’s beginnings; this post will cover some features of ProtonMail’s premium plans: aliases and custom addresses, custom domains, multiple users, and more. Continue reading “ProtonMail Five Years Later, Part III: Security Features”

ProtonMail Five Years Later, Part II: Tiers & Paid Features

I have been using ProtonMail full-time for over five years, and recommending it for almost six. This blog is littered with references to it, along with several incremental updates. A lot has changed since ProtonMail’s beginnings; this post will cover some features of ProtonMail’s premium plans: aliases and custom addresses, custom domains, multiple users, and more. Continue reading “ProtonMail Five Years Later, Part II: Tiers & Paid Features”

ProtonMail Five Years Later, Part I: The Basics

I have been using ProtonMail full-time for over five years, and recommending it for almost six. This blog is littered with references to it, along with several incremental updates. A lot has changed since ProtonMail’s beginnings. This post will cover the basics of ProtonMail: how it encrypts your data-in-motion, data-at-rest, and some other features. Continue reading “ProtonMail Five Years Later, Part I: The Basics”

ProtonMail Two-Factor and Single Password Mode

Two days ago, ProtonMail released version 3.6. A number of new features were added in this release. The biggest one is long-awaited: two-factor authentication. Another new feature that interested me is ProtonMail’s new single password mode. Continue reading “ProtonMail Two-Factor and Single Password Mode”

ProtonMail Premium Review

Email is a service that we all rely on. Finding an email provider that promises a good balance of privacy, security, and convenience is a fraught proposition, however. As readers here doubtlessly know, I have huge privacy concerns around email. I hate giving out my real email address if possible, because it equates to attack surface (more on this later). I also hate using the same email for multiple services, but this creates major convenience problems. And I can’t store email with providers that either a.) dont’ store my data securely or b.) store it securely but scrape it for marketing purposes. Readers here also know I am a big fan of ProtonMail. This is why I decided to give ProtonMail Premium a try. Continue reading “ProtonMail Premium Review”

DIY Encrypted Email 4: In Practice

In Part I of this series we discussed the principles of rolling your own encrypted email.  Part II and Part III covered the installation and setup of the applications needed to make this happen.  Today we will begin talking about how to actually use all this “stuff”.  Installing the programs are the easiest parts of this process, but using it isn’t as daunting as it was just a few years ago.  Hopefully you have been using Thunderbird over the past week and have some comfort level with it. To begin using it to send and receive encrypted email, you will need someone to practice with.  This is a good reason and a good strategy to encourage others to use encryption!

Continue reading “DIY Encrypted Email 4: In Practice”

ITRH Interview & Bugout Backup

I haven’t written much about data backups here before, but they are incredibly important.  Everyday, run-of-the-mill data loss can range from frustrating to devastating. In the midst of a natural disaster the impact of personal data loss may be compounded as you are trying to deal with much more basic needs.  I am proud to be a guest on the In The Rabbit Hole Urban Survival Podcast this week (the episode will air today and can be found here).  Aaron and I talked about backing up the documents you may need to have on hand in an emergency, or what I call the “Bugout Backup”.  I also mentioned how to store and protect this information with encryption.  Our first topic was why having this information is important.

Continue reading “ITRH Interview & Bugout Backup”

DIY Encrypted Email 3: GPG and Enigmail

In the last part of this installment we discussed importing mail into the Thunderbird mail client.  Now that our email has been taken out of the browser, we can begin adding the cryptographic elements.  The first of these is GPG (Gnu Privacy Guard).  GPG is an open source implementation of PGP.  It will provide the actual encryption used for our emails. The next step is to install an add-on to Thunderbird called Enigmail.  Enigmail will provide the interface, allowing Thunderbird to use GPG’s encryption.  Installing and setting up GPG and Enigmail is the first order of business in this post.

GPG

Different operating systems require different versions of GPG.  If you are using Windows you will install GPG4Win.  If you are using OS X you will install GPG Suite.  If you are using Linux, you can probably skip this step because GPG comes standard with most distros.  If you do need to download it you can do so here.  After you have downloaded the application, begin the setup process.  You will be prompted to provide your administrator password and select a language.  After you have done so you should see screens depicted in the following screenshots.

On the third screen you will be asked which components of GPG you wish to install.  I generally choose to make my installation as light as possible.  I uncheck everything except “GnuPG” and the “Compendium”.  The other components provide powerful capabilities, but they are superflous for our purposes.

GPG and Enigmail

ENIGMAIL

The next step is to install Enigmail.  Since it is only a extension to Thunderbird this is an easy installation.  First, open Thunderbird.  Next, click the hamburger icon, and then click “Add-ons”.

GPG and EnigmailClick the search bar in the Add-ons menu and type “Enigmail”.

GPG and EnigmailClick install button for Enigmail.  It will begin downloading.

GPG and EnigmailAfter Enigmail is installed, you will be prompted to restart Thunderbird.  After a restart you will be ready to being creating your key pair.

GPG and Enigmail

CREATING A KEY PAIR WITH GPG AND ENIGMAIL

With GPG and Enigmail installed, you are ready to begin creating your key(s).  When Thunderbird restarts the Enigmail Setup Wizard will begin walking you through the process of key generation.  This is not an overly complicated process, and Enigmail will automate most of it.  With the “Start setup now” radio button checked, click “Next”.

GPG and EnigmailOn the next screen select “I prefer an extended configuration”.  On the next screen check “I want to create a new key pair for signing and encrypting my email”.  The next screen will prompt you to enter a password.  I recommend that you take some time to enter a good password.  This password can never be changed, so take the time now.  After clicking the “Next” the key generation process will begin.

GPG and Enigmail

After the keys have been generated you will be prompted to generate a Revocation Certificate.  A revocation certificate allows you to revoke your keys if they are compromised in the future (leading to compromise of communications encypted with them).  This ensures that if you lose control of your private key you can still maintain control of the communications.  We will discuss how to revoke a certificate in a future post on the topic.  Ensure you store the revocation certificate in a secure location.

GPG and Enigmail

Now that we have installed GPG and Enigmail and setup a keypair, we are ready to being exchanging encrypted emails.  We will cover this in the next segment, so stay with me!

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DIY Encrypted Email 2: Thunderbird

This is the second in a multi-part series on setting up your own email encryption.  Today we will cover installing and setting up Mozilla Thunderbird.  Thunderbird is a desktop mail client that allows you to access your email from a platform other than the browser.  This is a necessary step because of the vulnerabilities inherent in internet browsers.  Thunderbird is popular (I am far from the first person to post a Thunderbird tutorial) and capable.  For our purposes it will be used to remove email (and crypto) from the browser into a more secure environment. Continue reading “DIY Encrypted Email 2: Thunderbird”

DIY Encrypted Email 1: The Basics

As promised in my post on email threat models, today I am going to begin a series on DIY encrypted email.  As I discussed in the email threat modeling post, this is the most secure email encryption available.  Before we get into the “how to” portion of this, it is important to first understand asymmetric encryption. Email encryption relies on a wholly different encryption model than that used to protect data-at-rest.  Encrypting email and web traffic relies on asymmetric encryption (also known as public key cryptography).  One of the classic problems with encryption for communications is “key exchange”. It would be simple to encrypt  a PDF and email it to someone.  However, it would be difficult to exchange the password for that file without sending it unencrypted.  Sending it plaintext leaves the password vulnerable to interception.  This compromises the integrity of the entire system.  But there is a better way. Continue reading “DIY Encrypted Email 1: The Basics”